Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of the host-guest complex by using calixarene-based macrocy-cles (i.e., resorcinol-derived cyclic oligomers) with a good solubility profile can improve solubiliza-tion of hydrophobic drugs. Herein, we explore the ability of resorc[4]arenes to self-assemble in polar solutions, to form supramolecular aggregates, and to promote water-solubility of an isoflavone en-dowed with anti-cancer activity, namely Glabrescione B (GlaB). Accordingly, we synthesized sev-eral architectures featuring a different pattern of substitution on the upper rim including functional groups able to undergo acid dissociation (i.e., carboxyl and hydroxyl groups). The aggregation phe-nomenon of the amphiphilic resorc[4]arenes has been investigated in a THF/water solution by UV– visible spectroscopy, at different pH values. Based on their ionization properties, we demonstrated that the supramolecular assembly of resorc[4]arene-based systems can be modulated at given pH values, and thus promoting the solubility of GlaB.

Exploring the assembly of resorc[4]arenes for the construction of supramolecular nano-aggregates / Buonsenso, F.; Ghirga, F.; Romeo, I.; Siani, G.; Pilato, S.; Quaglio, D.; Pierini, M.; Botta, B.; Calcaterra, A.. - In: INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. - ISSN 1661-6596. - 22:21(2021), p. 11785. [10.3390/ijms222111785]

Exploring the assembly of resorc[4]arenes for the construction of supramolecular nano-aggregates

Buonsenso F.;Ghirga F.;Romeo I.;Siani G.;Quaglio D.;Pierini M.;Botta B.;Calcaterra A.
2021

Abstract

Many biologically active compounds feature low solubility in aqueous media and, thus, poor bioavailability. The formation of the host-guest complex by using calixarene-based macrocy-cles (i.e., resorcinol-derived cyclic oligomers) with a good solubility profile can improve solubiliza-tion of hydrophobic drugs. Herein, we explore the ability of resorc[4]arenes to self-assemble in polar solutions, to form supramolecular aggregates, and to promote water-solubility of an isoflavone en-dowed with anti-cancer activity, namely Glabrescione B (GlaB). Accordingly, we synthesized sev-eral architectures featuring a different pattern of substitution on the upper rim including functional groups able to undergo acid dissociation (i.e., carboxyl and hydroxyl groups). The aggregation phe-nomenon of the amphiphilic resorc[4]arenes has been investigated in a THF/water solution by UV– visible spectroscopy, at different pH values. Based on their ionization properties, we demonstrated that the supramolecular assembly of resorc[4]arene-based systems can be modulated at given pH values, and thus promoting the solubility of GlaB.
File allegati a questo prodotto
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/1584935
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 0
  • ???jsp.display-item.citation.isi??? 0
social impact